


He wears short skirt

by viruskit



Category: Supernatural
Genre: Cock Cages, Confused Dean, Deepthroating, Face-Fucking, Feminization, M/M, Public Blow Jobs, Size Queen Castiel, Teasing, Twink Castiel, semi public blowjobs
Language: English
Status: Completed
Published: 2016-05-12
Updated: 2016-05-12
Packaged: 2018-06-08 01:21:15
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,017
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6833077
Author URL: https://archiveofourown.org/users/viruskit/pseuds/viruskit
Summary: <blockquote class="userstuff">
              <p>Dean takes the train and sees a gorgeous girl with an amazing ass and she wears short skirts every day. Only that girl is actually a guy and that makes Dean even more interested in him.</p>
            </blockquote>





	He wears short skirt

**Author's Note:**

  * For [TheBeastsWrite](https://archiveofourown.org/users/TheBeastsWrite/gifts), [thelonelywriter](https://archiveofourown.org/users/thelonelywriter/gifts).



> I do love a BAMF Castiel but the only thing I can write is twink-y Castiel. I'm not at all mad

Dean Winchester stood at the train stop completely bored. He could honestly get to work faster if he took his car but lately the train seemed like a better choice. Not because was saving money getting, or because taking the extra 10 minutes to walk to work was a bit of good exercise for him but because of the gorgeous young man who near constantly wore skirts every day.   
It all started when Dean’s beloved Impala broke down one day and he had to take it to his uncle Bobby’s to get it fixed. The only way he could get to his new job at Sandover and back was with public transport and for the first 5 minutes on it he regretted not getting a rental car. The sixth minute on the train he saw a dark haired beauty get on the train with a barely there skirt. Dean could just see the curve of her round ass peeking out from the frilled skirt and it gave him something to look at for the next 30 minutes which made him happy.   
The next week the girl got on the train, faced away from Dean and was wearing skirts that showed off her ass in the best way possible; either the skirts were skin tight or short enough that they violated some sort of dress code. Either way Dean loved looking.   
It wasn’t until a tall, light haired man got on the train with her and Dean learned that she was actually a he. The boy in the skirt was asking the taller man about work at the hospital and if he should visit sometime. The blond man said no and asked the shorter man about school. “Cassie” was his name and he had a gravelly voice that sent shivers down Dean’s spine. Dean regretted that Cassie was dating the taller man but he never stopped looking at the plump ass in front of him.   
Today the train was running late and Dean was getting antsy. He honestly needed his daily fix of ass and not be late to work. Taking the Baby to work would have been faster but there wasn’t much to look at on the road. He began to wonder if Cassie was going to give up on the train and just walk to his destination. Dean would have by now. Then Dean’s thoughts disappeared when he saw that the train was coming.   
He got on the train, sat down in his usual seat and saw that there weren’t that many people on the train; probably because it was the start of a holiday weekend and most people were enjoying their time off. Six minutes in and he saw Cassie get on the train and for once the boy sat down. Across from Dean.   
Dean got a good look of the boy whose ass was the reason why his water bill was getting higher. The boy was gorgeous. He eyes that were a beautiful shade of blue, pink lips that looked slightly chapped, high cheekbones and a strong jawline but he still looked slightly feminine. Wearing the skirts helped too.   
So Cassie sat down across from Dean and didn’t bother crossing his legs. No, his feet were under the seat, uncrossed and Dean could see everything underneath. The boy was commando. It helped that the skirt was thin and Cassie was in the sunlight too because Dean could see the pretty pink cock cage the boy had on too.   
Dean groaned at the thought of that. The boy was gorgeous, dressed prettily and was *probably* a submissive and kinky? Dean would have loved to meet him somewhere else and wished Cassie was single.   
Thirty minutes passed and soon Dean had to get off the train so he could go to work and when he got up, Cassie got up too and headed out with him.   
Dean thought it was weird because the boy had never got off at this stop before. Not that Dean knew anyway; he always hurried off the train so he could get to work as soon as possible. Cassie quickly fell into step with Dean and they walked in silence for about five minutes.   
Dean was the first to speak up. “So, um, where are you going?” and quickly regretted it because he sounded like an old creep.   
“Sandover. My uncle works there and he wants me to intern there” Cassie smiled at Dean.   
Dean swallowed. What were the chances of them going to the same place at the same time?  
“Really? Who is your uncle? I might know him”  
“Zachariah Adler.” He said without even batting an eye.   
Dean’s boss’ boss was this kid’s uncle? Adler, who made most conservatives look like moderate liberals? What the hell was this boy doing in a frilly skirt and a fucking cock cage when he was going to his uncle’s job?  
“What’s your name?”  
“Dean. Dean Winchester.”  
“Castiel Novak-Alder. By the way, did you like the show?”  
Dean stopped. Show? What the hell was he talking about?  
Castiel stopped a step ahead and turned around with a smiled.   
“The show this morning. You know, with my skirt”  
Dean couldn’t believe what he was hearing. Castiel Adler was letting Dean look up his skirt. Was this a trap?  
Castiel’s smile started to fade and he started to look worried.  
“Shit. Luke told me that you were checking me out on the train. I assumed you were-“  
“Yes I loved the show, Cas. So much”  
Castiel looked relieved and his gummy smile returned.   
“Thank God. I thought I was teasing a straight guy. That would have been disastrous”  
Dean couldn’t believe his ears. This little punk was teasing him?  
Castiel’s eyes wandered down and his smile got wider. “Want me to take care of that?”  
Dean didn’t remember nodding (but he knew he did) and was pulled into a bush by the boy and his lower half was quickly undressed by Castiel who was now on his knees.   
“Fuck, that’s nice”  
Castiel rubbed the cock against his face and groaned. He pulled back and started kissing the shaft up to the head.   
Dean was loving this and started to rub Cas’ hair. He felt a soft tongue on the slit of his cock and bucked forward. It’s been a while since he’s gotten blown.   
Castiel was lapping at the cock, and blond hair popped into Dean’s mind.   
He jerked back and felt his hard cock hit his stomach. He saw that Castiel looked confused and slightly hurt.  
“Cas, what about your boyfriend? What would he say about you doing this?”  
Castiel squinted his eyes and tilted his head like a dog. “What boyfriend?”  
“Luke. The blond guy”  
Castiel smiled and started giggling which turned into full on laughter. “Luke’s my older brother, Dean. He’s the one who encouraged me to do this”  
Dean must have still looked shocked and Cas said, “I could call him if you want me to”  
Dean shook his head and walked forward to Cas so he could finish. He heard a soft “finally” before Castiel took the dick in his mouth and moaned around it.   
Cas was slowly taking the cock into his mouth and that was quite the feat. Dean was fairly well endowed and none of his partners get his cock down their throats but Cas seemed determined. He placed his hands on Dean’s thighs and after a few seconds he was to the base of Dean’s cock and his nose was in Dean’s pubes. He could feel Cas smiling around his cock before the boy pulled his head back.   
“Not bad, right?” he said winking at Dean, his lips a pretty shade of red now and glistening. “Dean, I want you to fuck my mouth, ok?”  
Did the train crash with Dean on it? Did Lucifer come out of hell and offer up his services in the form of a pretty twink who was blowing him within seconds of knowing him?  
He grabbed Cas’ head and dug his fingers into the soft, dark hair and looked down at the boy. Cas nodded and opened his mouth wide for Dean,  
Dean guided his cock into the warm and wet mouth and let out a heavy sigh. He’s never been able to do this and it felt awesome.   
His thrusts were shallow and he was mindful of the boy below. He was enjoying getting this deep for once in his life but wanted to take it slow with Cas just in case he couldn’t handle it. After a few minutes Castiel tapped on his thigh and he looked slightly peeved.   
His lips were redder than before and his cheeks were a bright shade of pink.   
“What the hell Dean?!”, he said and his voice was scratchier than before, “I said to fuck my mouth!”  
“I was, Cas. I just didn’t want to hurt you”  
“Dammit Dean I want you to fuck my mouth like you mean it. Really fuck it like you paid for it”  
Dean couldn’t believe that Cas wanted him to do it. “Are you sure, Cas? I could hurt you.”  
“I’ve done it before, Dean. I’ll be fine. Let’s move to that tree first though.”  
Cas sat with his back facing the tree and Dean moved in front of him. He was painfully hard now. Castiel kept eyeing his cock like it was his favorite meal.   
Cas was unbuttoning his shirt and Dean saw a flat chest with dusky pink nipples and wished he could play with them soon.  
He grabbed Cas’ head and once again guided his cock into the mouth. He braced himself with one hand on the tree and quickly bottomed out. He used his now free hand to hold Cas’ head in place while he started fucking forward.   
He aimed to the back of Cas’ throat and grunted. He was going crazy and the boy underneath him was taking it so nicely. Cas’ eyes were closed, tears prickling and he was moaning around Dean’s cock. Cas had one hand to brace him while Dean fucked and the other was pinching his hard nipples. He then saw Cas’ hand go down to his caged dick and tried his damnedest to get himself off that way.   
Dean couldn’t last too long; he was too excited and it’s been too long since he’s gotten any action. His thrusts were started to get erratic and his cock started hitting the inside of Cas’ jaw. He felt hands on his ass and Cas was all the way at the base of his cock. Dean didn’t even need to hold the boy in place when he came down his throat. Cas took t like a pro and pulled off Dean’s cock with a loud pop once Dean was finished cumming.   
Cas smiled, his lips a cherry red color and slick with spit. He wrapped his arms around Dean’s neck and kissed him deeply.   
“I’d like to do that again soon, Dean.” He said quietly.   
Dean smiled and kissed the boy’s forehead.   
“Same, baby.” He was just relaxing in the moment when Castiel cursed and told Dean that they were going to be late if they didn’t hurry. They both got dressed and ran to Sandover with a few minutes to spare. Once they got inside the elevator they smiled at each other and traded numbers. 

 

Dean found out that Cas lived close by with his older brother Luke and worked at a strip club as a bartender part time. His uncle wanted him to have a “real job” and not participate in the “sinful” acts that he thought Cas was out doing.   
Dean and Cas still took the train. Sometimes Cas would go pantyless and grind against Dean while the bus was crowded or stand in front of Dean while Dean could get a nice view of his ass. Sometimes they would get on the bus as early as possible so they could get to work as early as possible and fuck in Dean’s office or suck each other off in the bathroom.   
Dean had never been happier.

**Author's Note:**

> check out my tumblr viruskit.tumblr.com!!


End file.
